


Him.

by mehhchester



Category: Supernatural
Genre: Angst, Artificial Intelligence, Dirty Talk, Fluff, Future Fic, M/M, Smut, barely even, like two seconds brief, very very very brief f/m
Language: English
Status: In-Progress
Published: 2014-01-21
Updated: 2014-01-21
Packaged: 2018-01-09 12:07:16
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 7,925
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1145802
Author URL: https://archiveofourown.org/users/mehhchester/pseuds/mehhchester
Summary: <blockquote class="userstuff">
              <p>Dean Winchester lived by two rules: </p><p>1. Don’t take a joint from a man named Don.</p><p>2. Don’t trust technology.</p><p>So when his brother Sam trusts a new AI operating system, Angel Intellence System, onto him, his life gets turned upside down as his new ‘Angel’ leads him down a path of trust, friendship, and forgiveness.</p><p>(Loosely based on the movie Her.)</p>
            </blockquote>





	1. Agoraphobia

 

**Chapter Track: Agarophobia//Autoheart**

_"I am dented by the skies, they keep me up at night_

_It's not agoraphobia, it's just lack of air supply"_

 

Dean Winchester was not a punctual man.

It wasn’t that he enjoyed being late, but when you lived in a tiny one bedroom apartment near train tracks, one got used to loud noises and tended to block out any alarm, no matter how blaring.

His lack of punctuality was the reason he was now very late for work and standing in front of his very angry boss, Bobby Singer.

“Look boy, either you get an alarm clock that’ll actually get your lazy ass outta bed and into my shop, or it’ll be my foot up your ass every morning doin’ it.” No matter how close Dean was with the gruff older man, he knew Bobby wasn’t joking. Instead, he gave him a weak smile, nodded, and gathered up his tools for the day.

Working at Singer Salvage Yard had its moments. With all the technology today, there were very few actual human-run mechanics anymore. Most people chose instead to go to one of the many ‘car ports’ companies ran to have a computer-run diagnostic and repair of their car. Bobby didn’t trust these places. “A bunch of numbers on a screen can’t fix you better than two experienced hands can.” He often said after seeing the steadily decreasing income the shop was bringing in. Even if Dean agreed, he couldn’t help but think the small shop had maybe a good six months left under its belt before it closed from lack of money coming in. The thought was depressing to say the least.

But days like today made working there worth it. After a computer malfunction made the only car port in their small town flip a car over, completely wrecking it, people began streaming into the salvage yard to get their car fixed. Dean couldn’t help but notice Bobby’s smile from across the shop.

After fixing up the last car before lunch, Dean wiped his hands on his coveralls and went out to reception to have his daily break with the receptionist.

Calling Jo Harvelle an ordinary receptionist would be a grave insult, though, and would probably result in his ass getting kicked, Dean thought. At 5’3 and 105 pounds with long blonde locks, Jo looked like your average college girl, pretty and usually Dean’s type. However, Dean had known Jo since they were eight after she punched him in the stomach for saying she had cooties. They had been best friends ever since.

“Singer Salvage Yard, you’re gonna have to wait a second.” Jo said as Dean walked up to the desk, putting down her headset unceremoniously and hitting the mute button on her phone.

“You make a really shitty receptionist, you know that?” Dean snorted as he leaned against the desk. Jo just rolled her eyes and swatted him away. “Yeah, yeah. I’m the best damn thing that ever happened to Bobby, he’s not going to fire me.” She said as she stood. “And get your grease stained monkey suit off my desk. This is mahogany.”

Dean laughed and pushed himself off the desk, shoving his hands in his pockets. “I’m surprised you even know what wood looks like, your entire apartment is fucking chrome plated.” That earned him a punch to the arm and another eye roll.

“For one, it’s not chrome, it’s,” She paused. “Well fuck, I don’t know what it is. Doesn’t matter. Two, I’m sorry not all of us can live in the stone age with you, old man.”

There was a running joke in the garage that Dean should have been born in a different decade and it was probably true. He was never one for all the modern technology the world today offered. The newest thing he owned was his laptop, and that’s only because his brother Sam had brought it for his birthday and wouldn’t ‘take no for an answer, even if it means shoving the stupid thing down your throat’.

Their father, John Winchester, swore off anything that took more than two AA batteries until the day he died. After their mother’s death, John took his two sons on the road to get them away from the big city and Dean had fallen in love with the simplicity of things from days past. If that meant getting mocked, he could deal with it.

“Not my fault your brain ain’t big enough to work a tape player, blondie.” Another punch to the arm, harder this time, and the pair were off to the restaurant Jo’s mom owned.

Ellen Harvelle was the closest thing to a mom Dean was ever going to get. No nonsense, firm, and yet still somehow gentle, he loved her in the way he figures he would have loved his own mother if he ever got a chance to actually know her. That’s why he spent so much time at The Roadhouse, the bar and grill she owned. Besides the free food, Dean got a chance to make up for twenty-seven years of neglect and, if anything, he figured he at least deserved that.

“Dean Winchester, your butt gets scrawnier every time I see you.” Ellen quipped as the two walked into the bar.

“All the fat must be going to mines.” Jo sighed dramatically as she turned around to look at her butt.

“Must be.” Dean agreed, ducking to avoid a smack to the back of the head from her. “Come on, stop messing with my daughter and come gain a few pounds back. When’s the last time you ate food that didn’t come in a white styrofoam box?” Ellen gave him a knowing look as Dean sat on one of the barstools and tried to avoid her gaze. Working extra hours at both the garage and a beer brewery downtown didn’t exactly leave time for buying groceries, let alone cooking. Most of the time, Dean’s meals were greasy and technically ‘foreign’.

“Ah, you know cooking was never my thing. I was never a girl like Sam.” He said, flashing Ellen a grin. That only earned him a whack on the head with a can of beer. “You better watch your misogynistic mouth boy. Girls don’t gotta cook just cause we posses a vagina. Hell, I didn’t learn to cook till after Bill died for survival.” Ellen looked sad for a moment, making Dean feel like shit for making her think about her deceased husband, until she perked up again as her eyes landed on her daughter. “Speaking of girls though, I know one that’s about to get thrown out on the streets if she keeps trying to sneak boys in here at all hours of the morning. Do I look like I want to hear you when I’m tryin’ to sleep?”

Glad the attention was finally off of him, Dean laughed and leaned back on the bar, happy for his little family. He didn’t get moments like this growing up and for a while with a few exes, he thought he might start his own family, but time after time proved him wrong. At this point in his life, he was content with a good beer, a few laughs with his family, and work. That’s about as good as he thought it was getting for him.

///

“You can’t be serious Sam.” His brother made a face at him from the flicking translucent screen hovering in front of Dean showing that he was, in fact, serious. It was barely four o’clock and Dean was already pissed.

“Dean, no offense, but your life is a mess. This will be good for you! Besides, your birthday is coming up and you refused to tell me what you wanted. This is your own fault.” Sam brushed his annoyingly long brown hair out of his face, making Dean want to both hang up and grab a pair of clippers. He loved his younger brother, but ever since he moved to California for school, he had become increasingly soft and worse yet, bossy. Dean figured it was apart of the ‘becoming a lawyer’ territory.  

“Sam, no. I don’t need a damn… what, computer? Telling me what to do. No.” Sam sighed again, rubbing his palm over his face. “For the last time, they’re AI’s and they have bodies. Just like everyone else, they have a job. Theirs just happens to be running the lives of bastards like you. Besides, you won’t even see it. They just take over your computer and phone when you need them to.”

Dean really didn’t like this idea. The last thing he needed was some overly smart computer touching all his personal files and knowing his exact location at all times. His father would be turning in his grave if he knew. .

“I don’t know, Sammy.” Dean said, somewhat relenting. “Look, I already bought it and sent it to you. Just try it out. If you don’t like it, I’ll just return it and, I don’t know, buy you a pair of fuzzy dice instead.” Dean cracked a smile at that, reluctantly giving up. “Alright, bitch. I’m trusting you.”

“First time for everything, jerk.” Sam said back, giving his brother a wide grin. As much as Dean hated it, he could never say no to his brother. He had been taking care of him since the younger of the two was six months and the habit had never stopped. Sam had this infuriating trick where he’d pull these big puppy dog eyes and make his brother agree to do anything he asked, no matter how ridiculous. It was the reason Sam was currently in California and Dean was left alone back in South Dakota.

“Look, I gotta go. Next job starts in twenty. Try not to fuck up my life too much with ‘gifts’ anymore, would you?” Dean said, any real malice failing to transfer into his words.

“Yeah, got you. Try not to work so hard, would you?” Sam said, actually looking worried. Dean just rolled his eyes. They had this conversation every week and no matter what he said, Sam was never satisfied. Well, someone had to pay for his fancy law education and Dean refused to let it be Sam.

“Bye Sammy.” He said, hurriedly pushing the button on his earpiece that ended the call.

“A life organizer. The boy’s crazy.” Dean muttered to himself as he stood to get ready for another six hours of work.

///

It had been a long few hours at his second job at the local brewery. He was in charge of just basic maintenance, which meant fixing up the barrel machines, making sure the track line went along smooth, and other surely exciting tasks to someone who wasn’t Dean.

Unfortunately today, Dean ran into traffic and arrived five minutes late to a boss who absolutely hated anyone being tardy. His first twenty minutes of work were spent getting yelled at before being sent to the boiler room, the shittiest job of all.

In all, it wasn’t Dean’s favourite way to spend his night. Getting home at eleven usually meant just heating up whatever leftovers were in the fridge and calling it a night, but tonight he was tired, angry, and lonely.

That meant getting drunk and going to his favourite chat room to find someone to talk to. It was sad and probably a bit desperate, but Dean found out six months ago that finding people over the airwaves was a lot easier than finding people at bars and a hell of a lot easier to get rid of once he was finished.

Grabbing a bottle of whiskey from the cabinet, he sat down on his ratty couch, not bothering with a glass. After taking a big swig, he pressed the button on his earpiece. “Find women, aged twenty-five to thirty-five who are lonely.” Dean recited his usual preference to the chat room automated operator.

“Found, littlegirlred. ‘ _Hey. Uh, pretty new to this, pretty lonely. Looking for another girl to just-’”_

“Next.” Dean said, leaning back in his seat.

“Found, kalikitty. ‘ _Hey there big boys, I’m lonely and looking for someone to simply fucking ravage and maybe take a little blood along_ -’”

 “Next, dear jesus.” He definitely didn’t want any part of whatever that chick was offering.

“Found, bombshellbela. _‘Hey there. I’m just lying here, lonely, looking for someone to talk to and maybe warm up the other side of my big bed_.’”

“Stop. Send message.” The girl seemed okay enough and had a pretty sexy British accent that would do just fine for what he was looking for.

“Hey there. I’m sure I could find someway to liven up your bed. I hear I’m great company and warm to boot.” He always hated sending the reply messages, they always  sounded so forced and awkward

“Bombshellbela has accepted piecurious’ chat request.”

“Hey there.” Dean started off, already sliding off his pants. After months of doing this, he’d learned to start early.

“Hey there sexy. So piecurious, huh? Guess I’ll never has to ask you to choose between cherry and apple.” He forced a laugh at that. There was only so many times he  could hear a joke about his lame, drunkenly made username before he got tired of it.

“Yeah, I’m good with both. I’m sure you’re really a bombshell too.” The girl giggled and he could hear shuffling from her end. Good, Dean thought, she was getting ready too.

“You bet I am. It’s pretty sad no one is here to keep me company in my big bed.” She purred into Dean’s ear pierce. His cock twitched a little in interest at that.

“Yeah, I bet. If I was there, I’d make sure you were plenty distracted.” Dean said, beginning to slowly stroke his cock. “Oh yeah? How would you do that?”

“To start, I’d run my hands down your sides until my hands are resting on your ass. What’re you wearing?” At this point, Dean always felt like he was reading a script from a bad porno. It wasn’t exactly the most stimulating thing in the world, but it got the job done.

“Whatever you want sweetheart.” Internally sighing, he realized that most of the work was going to be coming from his end. “Right then. So you’re wearing that really sexy piece of lingerie I love, the green one. And my hands are on your ass, sliding their way around to your hips.” From the other end, Dean can hear small mewls and moans.

“Oh yeah darling, I want- I want you to taste me.” The british woman moaned out. “Alright then. So I lift up your lingerie, I’m trailing kisses down your stomach until-”

“Bite. Hard. Hard as you can.” Dean stopped for a moment, confused by the turn of events. “I’m sorry, you want me to- bite you?”

“Yes!” She cried out, sounding a bit annoyed. “Like a dog. A vicious, sexy dog.”

“Uh, alright? So, I bite down on you as hard as I can.” Dean felt beyond awkward now but didn’t know how to just end the chat. He had been apart of some weird kinks before -Rhonda Hurley came to mind- but never had someone asked him to viciously bite on their most sensitive area. It was a bit frightening to be honest.

“Now shake your mouth. Like a dog with a big steak in his mouth!” The woman’s cries were getting louder and it was clear she was getting close to coming. All the while, Dean watched his cock rapidly deflate at the mental image she was providing. He was pretty sure he’d be scarred for life after this.

“Yeah, I’m doing just that. As hard as I can.” He tried to picture other things to maybe get his head- and dick- back in the game. Lisa, his first girlfriend; Madison, his sexy neighbor; even the young checkout counter girl who always bagged his groceries for him came to mind. Nothing worked. He was done for the night.

After a few seconds of loud, and quite frankly scary, cries and shrieks, Dean heard heavy panting from the other end. “Wow, I came so hard.” She said, obviously quite proud.

“Yeah, same.” Dean lied. There was no point in telling the girl the truth,there was nothing she could do for him now.

“Okay, well, bye!” His earpiece beeped twice, alerting him that the chat had been disconnected.

 Well, that had been disappointing.

Dean angrily took the earpiece out of his ear, put his dick away, and took another big swig of his whiskey. There was no point in trying again, he was too upset and too traumatized. Instead, he booted up his laptop and started up one of the games he bought a while back. If Sam insisted he have the stupid thing, he might as well enjoy it. The bright blue translucent light shot up, showing the opening screen of the game.

It was simple really. He was a space explorer and had to explore the galaxy to find a way to save his home planet. Somehow though, he had gotten himself stuck in an underground cavern of caves and had been there for a week now. Every time he played, Dean became more and more frustrated with both the game and himself.

Tonight seemed to be no different. After an hour of wandering around in circles, Dean gave up and angrily turned the game off. He got up and trudged into his room, upset and completely done with the day. As he crawled into bed, he drifted off into a nightmare that involved a haunting robotic voice, his mother screaming, and fire.

///

The next morning, Dean woke up grumpy and covered in sweat. After a quick shower, he realized he had nowhere to go today since it was Saturday and he was off from both of his jobs.

Dean did not like being bored.

He got dressed anyway and headed down to check his mail. As predicted, a small box sat in his mail chute, sent from Sam. Dean figured he’d pay extra for express shipping, Sam was never good with managing money.

Eyeing the box wearily all the way back to his apartment, he sat down in front of his computer and just waited. He didn’t have to do this, not really. If Dean really wanted to, he could lie to Sam and tell him he tried it and hated it, and Sam would probably believe him. The thought of lying to his brother made him a bit uneasy though. He knew his younger sibling only wanted the best for him, even if it was a bit misguided at times.

“Alright, here goes nothin’.” Dean grumbled, opening the box and taking out the packing.It had white wings on the outside, a bright contrast to the blood red of the rest of it all. Angel Intelligence System sat out in big, bold letters, making Dean roll his eyes. The company that made this were probably a bunch of douches so he was already starting to hate their product.

Even if he was less than impressed with their packaging, Dean opened the box and took out the small chip and slid it into its port. Immediately, his computer screen turned all white, a shiny halo falling down from the top of the screen and spinning slowly as a loading screen.

Once more, Dean rolled his eyes.

“Hello, Dean Winchester!” A voice, Dean figured was supposed to sound angelic and graceful, said. “Welcome to the Angel Intelligence System. To make your perfect angel to perch on your shoulder, we need to know a few things about you.”

Dean was already weary of this thing. Sam didn’t tell him he was actually going to be making the damn thing. He should have researched what he was getting into some more.

“First off, what is your favorite color?” _Alright, easy enough_ , Dean thought. “Green.”

“Thank you! Secondly, what is your relationship with your mother like?” The voice carried on, sounding as if it could have been asking for the weather. “Oh. Uh, she’s dead. I think she was a pretty cool mom before she died though.” Dean said, scratching the back of his head awkwardly.

“Angel Intelligence Systems is very sorry for your loss.” It paused briefly before carrying on. “Would you say that you’re more prone to mornings or nights?”

“Nights, I guess, what does that have to-” The voice cut him off. “Would you prefer a male or female angel?”

Dean debated this for a moment. With his luck, he’d get a sexy sounding female voice and be constantly turned on by his… whatever this was supposed to be for him. “Male.” He said finally.

“Thank you.” The voice kept asking a series of questions, all more strange than the last. Finally, after about fifty questions, the voice finally said, “Thank you! Now processing your very own angel.”

Dean leaned back in his chair and sighed deeply. That was the most tedious thing he’s ever had to do, and he’s spent a day doing only oil changes. He definitely should have researched this more.

“Welcome, Dean Winchester, your angel Castiel!” The voice sounded way too excited for his liking but Dean was just glad the damn thing was done asking questions.

“What kind of name is Castiel?” Dean asked aloud.

“It’s the name chosen for me. I suppose if you really hate it, you may change it.” A deep gravelly voice came from his computer. Dean scrambled back in his rolling chair. “Holy shit, man. You sound… real.”

“Well, I am technically real on some level. Not on a physical level but that is only because I have no vessel as of yet. Of course-” Castiel rambled. “Dude, stop. Didn’t ask for a science lesson. So,” Dean paused, unsure of what to do now. “What are you supposed to be doing for me?”

“Most people choose to have their Angel organize their system, make appointments, and do general tasks for them, although I can do anything you ask if you give me a second to research it.” Castiel stated matter-of-factly. It honestly annoyed Dean a bit; he sounded way too smug, even for a computer.

“Alright, I guess we can start with the organizing files. My computer is a mess.” It was true, Dean had never been one for actually sorting through all his files. Unless it was porn, the one thing he actually bothered to keep up with after an awkward incident with Jo that he never lived down, files just kind of fell where they may.

“Very well. I see here that you have absolutely no sorting system here whatsoever.” Dean was taken aback by how blunt Castiel was. Weren’t these things supposed to be nice to you?

“Well, I have a life, KITT, so back off.” He shot back, annoyed. Dean could practically hear the confusion coming from Castiel.

“I’m afraid I don’t understand that reference, one second.” Dean rolled his eyes. Apparently, Angels don’t come built in with pop culture knowledge.

“Oh. That was an excellent television show. Albeit, a bit old and certainly incorrect about how artificial intelligence works.” Castiel said while Dean could see files being moved around on his desktop.

“Wait. In that second, you watched the entirety of _Knight Rider_?” Dean knew computers were good, but he was pretty sure that was impossible.

“It was point eighty-seventh of a second, but essentially, yes.” Castiel seemed entirely unimpressed with his feat, as if it was something he was used to. Dean supposed his programmers had made it so that it technically was.

“I have finished. I’ve opted to stay out of the folder marked ‘JoAnna Beth, keep your scrawny nose out of my things’, as I suppose you would not want my nose in it either. If I were to have a nose, that is.” Castiel deadpanned, snapping Dean out of his brief confusion. “Uh, yeah. Well, I guess that’s it for right now then. I really don’t have anything else for you to do.”

“Alright. Shall I sync to your phone as well so you may take me on the go?” Castiel asked. “Yeah sure, go for it.” Dean said as he got up from the desk, letting Castiel do his thing.

“Thanks Cas. For the file organizing, I mean.” He said, not even realizing he gave his new operating system a nickname.

“Is that another reference I don’t understand?” Castiel sounded very confused, making Dean laugh.

“Oh, no. It’s a nickname. No offense, but your name is kind of a mouth full.”

“Oh. I see. I do not mind it then.” Castiel said, sounding appeased. “Cool. Look, I’m going to go grab some food, so just… hang out. Make yourself at home in my… laptop, I guess.” Dean felt awkward, but he didn’t really know how to treat the artificial intelligence. It talked like a real, albeit weird, guy, but it was just a voice inside his computer. It honestly made him feel weird about the whole thing.

“Thank you, Dean. Have a wonderful day.” Castiel said before shutting the computer off. Dean grabbed his leather jacket and headed for the door, ready to go out and interact with real people. Maybe he’d go find an actual girl to bring home this time.

He definitely needed a break from technology, that’s for sure.


	2. Drain You

**Chapter Track: Drain You// Nirvana**

_"One baby to another says I'm lucky to have met you_

_It is now my duty to completely drain you"_

Dean Winchester did not enjoy romantic comedies.

So how he let Jo drag him to one, he’ll never know.

“Jo, the name of the movie literally has the words ‘Eternal’ and ‘Love’ in it unironically. Please tell me why you want to see this.” Dean said as they purchased their tickets.

She just shrugged her shoulders and shot him a grin. “Lead actor is hot, what can I say? He takes his shirt off more than you do in the summer and is nicer to look at. Sue me.”

Of course, Jo would be the type of girl to only see a movie because of an attractive cast member. Dean just rolled his eyes and stood in line to buy popcorn since their movie didn’t start for another twenty minutes.

“Hey, thanks for paying for this, by the way.” Jo rocked on her heels, not meeting Dean’s eye. He just looked at her for a second; he had no memory of agreeing to pay for anything.

“You’re a gold digger, you know that?” He grumbled, getting out his wallet as they neared the front of the line. She just laughed and elbowed him in the side. “I’ll finally put out if that makes you feel any better.”

Dean just rolled his eyes. For a hot second back in their sophomore year of high school, he had a crush on Jo which she adamantly didn’t return. As it turns out, as soon as he got over her, she began to develop feelings for him.

He was honestly kind of glad they never worked out, he was pretty sure they’d have killed each other by now.

“Yeah yeah, you harlot. If all it took to get in your pants was buttery popcorn and too expensive M&M’s, I’d have scored by now.” Dean said after they placed their order.

“You have a point Winchester. So,” Jo began and Dean knew he was in trouble. Whenever Jo wanted information or had some awful scheme, her sentence began with ‘so’. He’d learned to associate humiliation with that word by now.

“Oh no, Joanna Beth, don’t you dare ‘so’ me. Whatever you want to know, you can keep on wondering.” Dean grabbed their food and began to walk toward their theatre, only to be followed by a fast-walking Jo.

“Come on! You didn’t even hear what I was going to say.” She pleaded, her tiny legs somehow keeping in perfect step with Dean’s. If he didn’t know any better, he’d swear the girl turned superhuman when she wanted something.

Dean stopped and turned around, right outside the theatre’s doors. Somehow, Jo stopped in just enough time to not crash into him and smiled way too sweetly up at him. He was definitely worried now. “What is it, Jo?” He sighed.

“Yes! Okay, you seriously won’t regret this. I have this friend, her name is Charlie. And she’s a total sweetheart and saw your picture and just… kind of wanted to go out, maybe have a few drinks with you.” Jo ducked her head after her speech to avoid Dean’s glare, knowing too well it was coming.

“Becky. Rosen. That’s all I’m saying.” Dean huffed and walked into the theatre, leaving Jo behind.

The last time Dean agreed to go on one of Jo’s ‘blind dates’, which somehow only seemed to be blind for him, the girl that showed up was, well, insane. She spent half the night talking about this television show she was into and an apparently incestuous couple she liked on it before asking him if he had a brother. Answering that turned out to be even worse. Always one to show off his brother, Dean pulled out his phone and showed her a picture of Sam from a few months back.

From that picture alone, the girl was smitten.

She spent the rest of the date trying to find out everything she could about Sam, including his birthdays, hobbies, and if he’d ever be willing to go to Vegas. It was off-putting, to say the least. He finally had to buy her a cab and send her home after her eighth martini left her sobbing on the floor about how no one ever appreciated her and her talents.

That point on, Dean swore he’d never agree to one of Jo’s setups again.

Jo wasn’t set back by this though. “Okay, yes, she was a bad one. In my defense, how was I supposed to know Sam’s overly floppy mop was a lady woo-er now? You’ll be pleased to know, though, that Becky has found herself a writer. Apparently they write gay porn together.” She whispered excitedly all the way to their seats.

“Jo, no. I’m not even really in the mood to date right now. I’ve got a lot on my plate.” Dean whispered back, plopping down. That just got him a raised eyebrow.

“Busy? With what? No offense, but you have no friends but me. And having two equally shitty jobs does not count as keeping busy.” Jo said, shoving some popcorn in her mouth before Dean swatted her hand away.

“Will you at least wait until the movie starts? And just because I don’t have a full friend roster like you doesn’t mean I’m lonely. Also, my jobs are not shitty and I’m telling Bobby you hate your job and don’t want it anymore.” Jo just waved her hand dismissively.

“He already knows I hate it there. Would be hard not to. And back to my main point Winchester. Is this because of Cassie? Because that girl was a life-force sucking bitch and that’s coming from-” Luckily, an angry movie-goer cut her off with a loud ‘shush’. Jo shut up, but not before flipping the guy off.

Dean just sat back and opened his package of Red Vines, beginning to chew on one nervously.

Cassie was the last girl he ever seriously dated. She was warm, kind, funny, beautiful, and pretty much everything Dean wanted in a girl. For a while, he seriously considered proposing to her and just settling down. But then everything happened with his dad - _nonononotthinkingaboutthat_ \- and she decided his family was too crazy to deal with and left. According to everyone he knew, it was the best thing that ever happened to him.

Dean, unfortunately, couldn’t see it that way.

Jo leaned over to him so her head was resting on his shoulder. “Look, just think it over. I’m not asking you to marry her, just show her a good time. She’s a good friend of mine, I really think you’ll like her.” He just nodded and pointed to the starting movie, indicating the conversation was over.

She smiled and leaned back, grabbing more popcorn and shoving it all in her mouth.

There was a reason Dean didn’t like romcoms.

///

Dean trudged out of the movie theatre, feeling dirty from that god awful movie. “Remind me never to see another movie with you, okay?” He grumbled. Jo laughed and slapped his shoulder.

“Sure thing hot stuff. Look, I gotta go. Apparently I’m a hot commodity today.” Jo looked at him for a second, her face softening. “Just… give it a chance. I just want you to be happy.”

Damn it. Dean couldn’t say no now, not with her looking up at him with big, sad eyes. He needed to find people to hang with that weren’t so persuasive. “Fine, fine! Just, stop looking at me like that. It’s creeping me out.”

“Love you too, you big softie. See you later dork.” Jo slapped his ass and went on her way, leaving Dean to shake his head at her. She was like the little sister he was glad he never got. He couldn’t even imagine having to deal with both Sam and her in one house.

As Dean walked through the parking lot, he realized he let Jo drive him here (“If I’m going to see this damned thing, I’m sure as hell not wasting gas on it.”). So now she was gone and he was stuck. “Goddamnit Jo!” He yelled to no one in particular.

Well, he’d need a cab now. Dean pulled out his phone and thought about something. If Cas was on his phone, then surely he could help him. After he got home yesterday from a day at The Roadhouse with Ellen, who insisted on shoving half her menu down his throat and had him take the other half home with him, he was too tired, and a bit too weirded out, to actually test out further his new Angel.

Now was a good as any, he supposed. He put in his earpiece and pushed the button on the side, bringing his phone to life. “Uh, Cas?”

“Hello Dean. What may I do for you?” Castiel’s deep voice replied, making Dean shiver. How the company made such a realistic sounding voice, he would never know.

“Can you flag down the nearest cab for me? I’m kind of stuck at-” Castiel cut him off. “The movie theatre exactly three miles from your home, yes, I know. There’s a cab a block away from you, I’ll direct the driver to your location.”

There it was, the creepy factor of having this thing. His dad has raised him on a pretty strict ‘technology is evil’ regime, going as far to ban cellphones for the first eighteen years of Dean’s life. The idea that technology was eventually going to screw him over never quite left him, even after Sam left for California to be a Computer Science major. The ensuing argument about his choice of career had been his dad’s and Sam’s biggest ever and resulted in Sam walking out and being told to never return.

It took months to actually get his brother to talk to him again, and even then he made Sam promise to never actually tell him what his major entailed.

Therefore, it was probably going to take some time for him to actually get used to this seemingly all-knowing piece of technology.

“Dean?” Castiel said, snapping Dean out of his thoughts. “The cab should be there in about five minutes. Is there anything else you need?”

Dean shrugged before he realized who he was talking to couldn’t actually see him. “No, not really. So, what have you been up to man?” He asked. If he was going to do this, he was going to treat Cas like a real guy. It lessened some of the guilt he was feeling for letting technology become a part of his life like this.

“Oh.” Castiel seemed genuinely surprised by the question. “Well. I have been learning more about the world. I particularly like the bee. It’s fascinating how much honey they can produce.” Dean cracked a smile at that. Cas sounded so earnest that it was hard to be weirded out that he was talking about bees like they were something new and fascinating to him, although Dean supposed they were.

“Cool, I guess. I mean, I guess bees are pretty cool. I never really paid much attention to them.” Dean said, rocking on his heels as he waited for the cab. He wished he had brought a jacket with him; the cold October air was finally starting to get to him after being outside for an extended period of time.

“You should! Did you know that honeybees do not know how to make honey at birth? The more experienced bees teach the younger ones. I appreciate that sort of camaraderie.” For a second, Castiel seemed to actually sound sad but if there was one thing movies taught him, it was that computers don’t have feelings. Of course, most of his knowledge came from old, turn of the century flicks that depicted anything even slightly robotic as evil overlords, so times could have changed.

Before Dean could respond, a cab pulled up in front of him. “Well, looks like my ride is here. Talk to you later Cas.”

“Goodbye Dean.” Dean pushed the button on his earpiece and climbed into the cab, sighing heavily. He just remembered he still had to go into the garage later, which meant seeing Jo and getting what was to undoubtedly another spiel on her ‘super wonderful friend’.

He really did need other friends.

///

As Dean trudged into his apartment and plopped down, his earpiece beeped again. “Sorry to disturb you, Dean, but someone named ‘Jo’ just called and left a message. Apparently you have a date tonight, which I have scheduled for you, and she said she’s given you the night off of work.” Castiel paused. “She also, erm, wanted you to call and tell her all about the hot piece of voice you have taking messages for you.”

Dean was torn in between laughing and throwing something. Of course Jo would schedule a date for him and not tell him until the day of so he couldn’t back out. He was going to give her an earful when he saw her next. “Thanks, Cas.” He rubbed his palms over his eyes, suddenly very tired.

“Is Jo your girlfriend? I can send her roses if you’d like. I’ve just researched mating rituals and apparently that is very common.” Dean actually did laugh at that. “Hell no. Try annoying best friend. If you’re going to be sending her anything, try a bag of dog poop lit on fire.”

Castiel let out a nervous chuckle. “Is that something you actually want? There’s a company here that-” Dean sighed.  _Note to self_ , he thought,  _no sarcasm with Cas_.

“No, dear jesus. Sarcasm Cas, can you research that?” He said, opening his laptop on his coffee table where he’d left it that morning.

“I did. I’m afraid knowing the mechanics of it and actually getting it are two entirely different things.” Castiel sighed, making Dean feel bad for him. The poor schmuck had only been alive for less than twenty-four hours and already Dean was making him feel bad. Seems to be the only thing he was good at these days.

“Alright, look. How about you help me get through this part of the game that I’m playing? It’s kicking my ass.” Dean offered as he booted up the game.

“I can do that, sure.” Castiel eagerly replied, seemingly pleased to have found something he could help with. After five minutes of watching Dean play, Cas finally said, “Well, you’re going in a circle, for one.”

“What? I am not.” Dean defiantly replied. “Yes, you are. Look. Turn around and take the left tunnel this time. It’s the only one you have yet to try.”

“I’ve tried every damn tunnel in this joint, there’s no way- Oh.” Dean said as he approached a new entrance. “Told you.” Castiel sounded way too smug, but Dean couldn’t help but be appreciative.

“Yeah, yeah. Guess I owe you a thanks.” Dean said as his onscreen character approached a little virtual bot. He was short, all white, and although Dean would never say this aloud, kind of cute. “I think you’re supposed to talk to him.” Castiel offered, obviously trying to keep up his helpful streak. “Yeah, got that, thanks.” Dean rolled his eyes.

“Hey, little guy. Can you lead me to my spaceship?” Dean said, speaking for his character. The little virtual character beamed up at him, the screen closing in on his face when suddenly,

“Fuck you.” Said the tiny bot in the most chipper voice Dean had ever heard.

“Oh my.” Castiel said, obviously trying not to laugh.  _Since when did computers have a sense of humor?_  Dean briefly wondered before focusing back on his game. He had a rude fucker to deal with first. “What the- hey, fuck you man!” Dean retorted back angrily. What kind of game was this?

“Fuck you too!” The bot replied back, chipper as always. Seemingly happy with his response, the little white character led Dean to his broken down spaceship. “Thanks for nothing, you twat.” Dean grumbled while the bot just giggled. He was going to punch Sam for ever recommending this game to him.

“Dean, not to disturb you, but your date is scheduled to start in two hours. Perhaps you should get ready?” Castiel said over the game.

“Who that’s, your boyfriend?” The virtual bot tittered, tickled by the very thought. “No, asshole, he’s not.” Dean snapped, angry at the annoying little thing now following him around.

“You sure? You sound like you take it up the ass. I bet you’re the twinkiest of twinks.” The white little bot said, making obscene thrusting gestures. It was disconcerting to see something so cute doing something so vulgar, and if Dean wasn’t the one being insulted, he’d probably laugh.

“Oh my.” Castiel said for the second time that night, this time sounding much more embarrassed. “You looked up what a twink was, didn’t you?” Dean deadpanned.

“Yes. It wasn’t it my memory banks and I… well. Anyway. Your date, Dean.” Castiel reminded him once more.

“Yeah, I heard you the first time. Did Jo manage to tell you anything about this chick other than the fact that I’m meeting her- where exactly am I meeting her anyway?” Dean said, giving the tiny bot the bird after he tripped Dean’s character up.

“Well, her name is Charlie Bradbury,” Cas began, putting up images on the screen of a redheaded girl who seemed to really enjoy nerdy tee-shirts.

“She looks like a lesbian!” The bot cried out, plopping down on the floor of Dean’s virtual spaceship to stare up at the images.

“Shut the fuck up… what the hell am I supposed to call you anyway, asshole?” Dean said, glaring at his new unwanted companion.

“Trickster, bitch! Or Loki. Or Gabriel. My programmers were pieces of shit who couldn’t agree on a name.” The bot giggled again, amused at this for some reason.

“I like the name Gabriel. It is also an angel name. I think that my creators also produced this game.” Castiel said, putting up new info about Dean’s date on the screen.

“Gabriel it is then. Gabriel, shut the fuck up. Cas, whaddya got?”

“Well, there’s really not much on her. Apparently she’s works in the computer science field, although I couldn’t tell you where. She enjoys old pop culture hits such as Doctor Who and Star Wars, and is a natural redhead.” Castiel supplied. After a brief pause, he added, “She seems nice.”

“Bullshit on the natural redhead thing. I bet the curtains don’t match the drapes. And I still say she’s a lesbian.” Gabriel giggled again, now running around in circles like a deranged child.

“Last chance to shut up before I throw you into outer space.” Dean warned him angrily before shifting his eyes back up to the redhead on the screen.

Castiel was right, she seemed nice enough and had similar enough interests where there probably wouldn’t be any of those first date awkward pauses. He could still hear Cassie’s voice in the back of his head though ‘ _notgoodenoughnevergoodenoughinsanesofuckingcrazywhybotherwhywhywhy_ ’ and it was impossible to shake.

What if he got there and actually really liked this girl and she hated him? It wasn’t too farfetched of an idea. Sure, Dean knew he was good looking, but other than that, he had shit to offer. He was thirty-one and still living in an one-bedroom apartment that was haunted by the ghosts of a little brother who couldn’t deal with him and a dad who never loved him enough.

Who would want that?

“Dean…” Castiel said as if he was approaching a skittish animal. “I can cancel the date if you want. You don’t have to go.”

Dean sighed. As much as he would love to have Cas cancel for him, he wasn’t going to stand the poor girl up. It wasn’t her fault Jo didn’t give him enough time to make up a proper excuse. “Nah man, that’s fine. Thanks though. I guess I should get ready.”

“Don’t forget to bring lube! It hurts if you let her go in dry!” Gabriel said, grinning up at the screen. “Fuck you man. I hope you die at the end of the game.” The bot pouted before Dean shut the laptop.

After a pause of awkward silence, Castiel finally spoke up. “It’s a pretty casual place, a coffee shop called Grindr. If you’d like, I’m equipped to help you pick out clothes.”

Dean thought this over for a beat. He really didn’t have much fashion sense, what was the harm in letting someone who probably had the entire history of fashion in his head pick out his clothes?

“Alright, sure.” Dean shrugged. “If you just pick up your phone from the table, I can turn the camera on and see-” Castiel started before Dean hurriedly cut him off.

“Woah, you can just cut the camera on at will?” He said, suddenly not okay with this idea at all. “Dean, I would never cut the camera on without explicit instructions from you. I am programmed to need consent from my owner before I do anything that might infringe on their privacy.” Castiel said, sounding earnest.

Biting his lip, Dean nodded. “Two rules. One, never call me your owner again. I’m not running a plantation here. Just call me your… user, or something. Two, if I ever catch you watching me without my permission, I’m deleting you and then throwing both my laptop and phone out. Understand?”

“Understood, Dean. Now, shall we get you ready?” Castiel asked, obviously trying to quickly change the subject. “Yeah, guess so.” Dean picked up his phone and the light of his camera blinked twice, alerting him that it was on. He turned it to face him and waved awkwardly. “Hi, I guess.”

Castiel seemed to pause and then, “You have a lot of freckles.” He said simply. “Alright, let us go.”

Dean turned the camera around so Cas couldn’t see his blush.

He’d analyze later why that made him blush at all.

**Notes for the Chapter:**

> For all those wondering, Charlie is still completely a lesbian. I don't think I could seriously make her a love interest for Dean if I tried.
> 
> Anyhow, thanks for reading :)

**Author's Note:**

> So this is not beta-d, so if anyone wants to, please do message me and I'll love you forever. Any corrections anyone sees in the meantime, lemme know and I'll fix them.


End file.
